Purpose: Comfort is a vital component of orthosis therapy. The purpose of this study was to examine what features of orthoses (design or hardness) influence the perception of comfort by using previously established footwear comfort measures: 100-mm visual analog scale (VAS) and ranking scale. Methods: Twenty subjects were consecutively allocated to two experiments consisting of five sessions of repeated measures. Comfort measures were taken from four prefabricated orthosis in each session using the VAS (experiment 1) and ranking scale (experiment 2). Subjects in experiment 1 were also asked to rate each orthosis relative to their shoe using a criterion scale. Measures were taken in both walking and jogging. Results: A soft-flat orthosis was found to be significantly more comfortable than all contoured orthoses, including one of the same hardness using both the VAS and ranking scale. Using the VAS, differences between the soft-flat and contoured orthoses were also found to be clinically meaningful for dimensions of overall comfort and arch cushioning (>10.2 mm). Perceived comfort of orthoses significantly differed between walking and jogging on the VAS but was not clinically meaningful. Comparisons between the VAS and criterion scale detected a VAS difference of 11.34 mm between orthoses judged as comfortable as my shoe and slightly more comfortable than my shoe. There was a VAS difference of 17.49 mm between orthoses judged as comfortable as my shoe and slightly less comfortable than my shoe. Conclusions: Healthy subjects prioritize contouring over hardness when judging the comfort of orthoses. Clinically meaningful changes were required to change or enhance the comfort of orthoses standardized in material type and fabrication.